J.Crew's Head Stylist Names the Holiday Shoe of the Season — and It's Not a Heel

"Sizing up, doing slightly oversize silhouettes with one another — like a billowing, oversize trouser with an oversize men's shirt and a more refined velvet shoe. That kind of thing just feels easy. Also, mixing your tweeds and plaids and adding feminine accents — dusty pinks, blush colors, and mint. Those soft colors are really nice off of the traditional menswear patterns."

Shop the Look: J.Crew Perfect Stewart Plaid Shirt ($78) and J.Crew Cameron Slim Crop Pant in in Tartan ($128)